In a swell with opposing wind waves of a shorter cycle, you get a very different result in an offshore condition. Generally, on the rare occasions that I've had to deal with this, I think you need to be able to adjust the distance between the main vessel and it's tow to match the conditions. Those conditions involve the wind speed, seastate (sometimes mixed), and the speed of the vessel, as well as whether you're motoring or sailing.

Some dingys do gain advantages from leaving the drain plug out -- and some don't really like that much.

If you have a cover on the dingy, it sometimes helps -- but other times it will conceal a problem until its too late to easily deal with it.

I have seen boats tow tenders accross pretty open waters (like Newport to Cape May, for example). Around Bays, from Chesapeake to Penobscot, it certainly is not uncommon. In the Chesapeake, where we have frequent summer thunderstorms, I remember an O'Day 30 which had it's dingy blown over the transom and into the main sail (before it mercifully left headed for the Smith Island west of the Potomac River).

That's just an extreme example in an extreme condition. I'm sure that sailors can go for years without an issue -- at least until they don't :^)

I have towed a dingy occasionally, I just prefer to put it away and not have it dragging for visual and functional reaons. If getting in and out of the dingy to gunkhole or go ashore with ease is an issue, then I understand why people do it. There is no questions that a multiday cruise with a dog on board makes it a lot more desireable. ;^))))